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Gregor Wolf has a diverse work experience spanning over several roles and companies. Gregor started their career as a Researcher at the Technical University of Berlin in 1986. Gregor then worked as a Consultant from 1989 to 1991 before joining Condat as a Software Project Manager for a year. From 1992 to 2001, Gregor served as the Director at Klopotek & Partner GmbH. In 2001, they became the Managing Director at The BtoB Company. Gregor later returned to Klopotek & Partner GmbH as Managing Director from 2003 to 2013. During this time, they also held the position of Chief Technology Officer from 2004 to 2013 at Klopotek AG. Gregor then joined OPTIMAL SYSTEMS Gruppe as Director Product Management from 2013 to 2015. Gregor also served as the (Interims) Director Software Development for a brief period in 2014. From 2015 to 2022, they held the role of Chief Operating Officer at OPTIMAL SYSTEMS Gruppe. Since April 2022, Gregor has been the CEO of OPTIMAL SYSTEMS Gruppe.

Gregor Wolf attended Technische Universität Berlin from 1980 to 1985, where they completed a degree in Informatik.